I just bought a 60GB iPod Video and am having several issues with the sync:
I selected to sync all files and playlists. However, the only playlists that actually sunc were the MC defaults (i.e.: Recently Imported, Recently Played, Recently Ripped and Top Hits, but none of the MC playlists that are in Playlist Groups). All of my personal playlists that I've made did not sync. However, all of my playlists that I've made are organized in Playlist Groups.
I then tried putting these playlists into the sync que and when I attempt to sync I get the message from MC "None of the tracks can be transferred. Common errors include insufficient rights or unsupported file types."
I have yet to install iTunes or even attempt to use it as I want to use MC exclusevely, but I am running out of ideas to make it work. If I Reinitialize the iPod it'll work again, for one sync only. I have also tried the sync option where I select the playlists and that won't work either.
Please help.